title: Simple and direct sp3 C-H bond arylation of tetrahydroisoquinolines and isochromans via 2,3-dichloro-5,6-dicyano-1,4-benzoquinone oxidation under mild conditions.
abstract: The 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated sp(3) C-H bond arylation of tetrahydroisoquinolines and isochromans is described. The corresponding products were facilely synthesized via a simple nucleophilic addition reaction between readily available aryl Grignard reagents and iminium (or oxonium) cations generated in situ by DDQ oxidation of tetrahydroisoquinolines (or isochromans) under mild conditions.
authors.affiliation: Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki, Nagasaki 852-8521, Japan. muramatu@nagasaki-u.ac.jp
authors.forename: Wataru
authors.initials: W
authors.lastname: Muramatsu
authors.forename: Kimihiro
authors.initials: K
authors.lastname: Nakano
authors.forename: Chao-Jun
authors.initials: CJ
authors.lastname: Li
mesh_terms: D016227:Benzoquinones / Q000737:chemistry*; D002384:Catalysis; D002839:Chromans / Q000737:chemistry*; D006860:Hydrogen Bonding; D007202:Indicators and Reagents / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D044005:Tetrahydroisoquinolines / Q000737:chemistry*
chemical_list: D016227:Benzoquinones; D002839:Chromans; D007202:Indicators and Reagents; D044005:Tetrahydroisoquinolines; C000928:dichlorodicyanobenzoquinone